Brown dye and process of making same.



' NIT-TED STATES PATENT omen.

KARL SCHIRMAOHER, OF HCCHST-ON-THE-MAIN, GERMANY, ASSIGNOR TO THEFARBWERKE, VORMALS MEISTER, LUOIUS d BRUNING, OF SAME PLACE;

BROWN DYE AND PROCESS OF MAKING SAME.

SPECIFICATION forming part of Letters Patent No. 647,236, dated April10, 1906.

Application filed January 24,1899. Serial No. 708,279. (Specimens) Toall whom, it may concern:

Be it known that I, KARL SoHIRMAcHER, Ph. D., a citizen of the Empire ofGermany, residing at Hochst-on-the-Main, Germany,

5 have invented certain new and useful Improvement-s in the Manufactureof Brown Dyestuffs for Wool, of which the following is a specification.

I have found that by the action of diazotized nitro and sulfonicderivatives of ortho amidophenol-such as 1:2:3z5 and 1:2:5:3nitroamidophenolsulfonic acids, picramic acid, oramidophenolsulfonic-acid upon metaphenylenediamin ormeta-toluylenediamin or their sulfonic acids new brown dyestuffs may beobtained which are valuable for properties superior to those of otherdyestuffs. If wool be dyed with these coloring-matters and subsequentlytreated with bichromate, then the intensity of shade increases and thedye is characterized at the same time by snperior fastness. Theexistence and position of the hydroxyl in these dyestuffs appear to beof greatinfluence, as'similarly-formed dyestuffs not containing thisgroup or containing it in a different position cannot be obtained in thesame manner in equally fast shades.

The process is illustrated by the following examples:

Example I: 23.4 kilos of nitroamidophenolsulfonic acid are diazotized bymeans of thirty-two kilos of hydrochloric acid and 6.9 kilos of sodiumnitrite, and the product is introduced into a solution of 10.8 kilos ofmetaphenylenediamin and twenty-six kilos of sodium acetate. The dyestuffis formed at once, and after being allowed to stand for a short time itis salted out. It is in the form of a greenish-brown powder soluble inwater 40 with a brown-red and with a somewhat more yellow color in watermade alkaline. The solution in concentrated sulfuric acid is yellow red.

Example II: 19.9 kilos of picramic acid are diazotized in the usualmanner and introduced into an aqueous solution of 18.8 kilos ofmetaphenylenediaminsulfonic acid and twenty-six kilos of sodium acetate.After standing for twelve hours the dyestuif is salted out. It is in theform of a brown powder soluble in water with a red-brown color, which onaddition of alkalies becomes more yellow. The solution in concentratedsulfuric acid is carmin-red. I

Example III: 18.9 kilos of 1:2:5-amidophenolsulfonic acid are diazotizedwith thirty kilos of hydrochloric acid and 6.9 kilos of sodium nitrite.The diazo solution is then poured into an aqueous solution of 12.2 kilosof meta-toluylenediamin and twenty-six kilos of sodium acetate andallowed to stand for from two to three days while being well stirred,the formation of the dyestuif proceeding slowly. The dyestuff on being,salted out and dried in the usual manner is in the form of a brownpowder soluble in water with a brown color. Its tint does not change onaddition of alkali. The solution in concen* trated sulfuric acid isbrown.

Example IV: 19.9kilosof picramicacidare 7o diazotized and the diazocompound is introduced into a solution of twenty one kilos ofmeta-toluylenediaminsulfonic acid and twenty-six kilos of sodiumacetate. After standing about twelve hours the dyestuff is salted outand filtered. WVhen in a dry state, the dyestuff is in the form of abrown powder soluble in water with a reddish-brown color and in sulfuricacid with a brownish-yellow color.

Addition of alkalies only slightly changes the tints of the aqueoussolution, which becomes a pale yellow.

Having now described my invention, what I claim is- 1. Theherein-described process for the manufacture of brown dyestuffs forwool, which consists in diazotizing and combining herein-describedderivatives of ortho-amidophenol with meta-diamins and their sulfonic oacids, substantially as described.

2. The herein-described process for the manufacture of a brown dyestufffor wool, which consists in combining diazotized picramic acids withmeta-phenylenediaminsulfonic acid, substantially as described.

3. As a new product, the dyestuif obtained In testimony that I claim theforegoing as] from picramic acid and meta-phenylenedimy invention I havesigned my name in pres aminsulfonic acid,beingabrown powder,soluence oftwo subscribing witnesses.

ble in Water with red-brown color, which, on KARL SCHIRMAOHER.- 5addition of alkalies becomes more yellow, the Witnesses:

solution in concentrated sulfuric acid being HEINRICH HAHN,

carmin-red. ALFRED BRIsBoIs.

